GB642255A - Lubricating compositions - Google Patents

Lubricating compositions

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Publication number
GB642255A
GB642255A GB25976/47A GB2597647A GB642255A GB 642255 A GB642255 A GB 642255A GB 25976/47 A GB25976/47 A GB 25976/47A GB 2597647 A GB2597647 A GB 2597647A GB 642255 A GB642255 A GB 642255A
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GB
United Kingdom
Prior art keywords
methyl
dihydroxy
epoxy
isopropoxypropane
chloride
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB25976/47A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bataafsche Petroleum Maatschappij NV
Original Assignee
Bataafsche Petroleum Maatschappij NV
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Publication date
Application filed by Bataafsche Petroleum Maatschappij NV filed Critical Bataafsche Petroleum Maatschappij NV
Publication of GB642255A publication Critical patent/GB642255A/en
Expired legal-status Critical Current

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    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/22Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
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    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M3/00Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/12Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/12Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/24Epoxidised acids; Ester derivatives thereof
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    • C10M2209/02Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/04Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an alcohol or ester thereof; bound to an aldehyde, ketonic, ether, ketal or acetal radical
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    • C10M2209/02Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/06Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an acyloxy radical of saturated carboxylic or carbonic acid
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    • C10M2209/02Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/06Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an acyloxy radical of saturated carboxylic or carbonic acid
    • C10M2209/062Vinyl esters of saturated carboxylic or carbonic acids, e.g. vinyl acetate
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    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10M2209/103Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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    • C10M2209/103Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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    • C10M2209/103Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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    • C10M2209/103Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/108Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified
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    • C10M2209/109Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/042Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
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    • C10M2215/06Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
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    • C10M2215/065Phenyl-Naphthyl amines
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    • C10M2215/20Containing nitrogen-to-oxygen bonds
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    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/042Sulfate esters
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    • C10M2221/04Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2221/043Polyoxyalkylene ethers with a thioether group
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    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
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    • C10N2020/00Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01Physico-chemical properties
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    • C10N2030/00Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/12Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
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    • C10N2050/00Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10Semi-solids; greasy

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
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  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Lubricants (AREA)

Abstract

Liquid polymers suitable as lubricants and having molecular weights from 150 to over 1500 are produced by heating at a temperature above 25 DEG C. in the presence of a catalyst one or more ethers containing (a) epoxide, or (b) glycol substituents, in case (b) to a temperature between 150 DEG and 300 DEG C. Ethers specified are (a) glycidyl methyl, ethyl, propyl, isopropyl, allyl, n-butyl, sec-butyl, tert-butyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, and dodecyl ethers; 2,3-epoxy-4-methoxybutene, -4-ethoxybutane and -4-isopropoxybutane; 1,2-epoxy - 3 - methyl - 3 - methoxypropane, - 3-methyl - 3 - butoxypropane, - 3,3 - dimethyl-3 - isopropoxypropane, - 3 - isopropyl - 3 - isopropoxypropane, - 2 - methyl - 3 - isopropoxypropane and - 3 - n - amyl - 3 - isopropoxypropane; and 4,5-epoxy - 6 - methyl - 6 - isopropoxyhexane; 1,2-epoxy-4-methoxybutane, -4-isopropoxy-butane, - 5 - ethoxypentane and 4 - methyl - 5 - tert-butylpentane; and 2,3-epoxy-5-isopropoxypentane; (b) 1,2-dihydroxy-3-methoxypropane and - 4 - isopropoxybutane, 2,3 - dihydroxy - 5-butoxypentane, 1,3 - dihydroxy - 4 - methoxybutane and 2,4 - dihydroxy - 5 - isopropoxypentane; 1,3 - dihydroxy - 2 - methoxymethylpropane and 1,4 - dihydroxy - 3 - isopropoxymethylbutane. Suitable catalysts for (a) are sodium and potassium hydroxides, stannic and aluminium chlorides and boron trifluoride and its ether complexes; for (b) are iodine, hydrogen chloride, bromide and iodide, sulphuric acid, p-toluenesulphonic acid, benzene sulphonic acid, sodium bisulphate, aluminium sulphate and potassium acid sulphate. Polymerization may be effected in liquid, solution, emulsion or gaseous phases. Methane, ethane, propane, butane, dihydronaphthalenes, cycloheptane, 2-methylnonane, 2,6-dimethyloctane, 2,2,3 - trimethyl - pentane, 2 - methyl - 3-ethylpentane, 2 - methyloctane, 2,4 - dimethylheptane, 4 - ethylheptane, dihexyl, 2,4,5,7-tetramethyloctane and water may be present. Additional reactants, e.g. methyl alcohol, ethylene glycol, amyl mercaptan, di-isopropylamine and bis-(b -hydroxyethyl) sulphide may may be present to react with the terminal hydroxyls. After removal of catalyst, the polymer is dehydrated, e.g. by distillation under reduced pressure and, if desired, decolourized by bleaching, hydrogenation using Raney nickel, nickel sulphide, copper, palladium or platinum catalysts, or percolation of a solution in benzene, toluene, xylene or hexane through fuller's earth. The terminal hydroxyl groups may be etherified by methyl bromide or iodide, ethyl chloride, propyl iodide, benzyl chloride, methyl-benzyl chloride, methoxyethyl chloride, sodium monochloracetate or allyl chloride in the presence of sodium hydroxide, liquid ammonia or quaternary ammonium bases or salts; or esterified with formic, acetic, propionic, butyric, hexoic, 2-ethylhexoic, lauric, stearic, myristic, palmitic and capric acids in the presence of sulphuric or phosphoric acids. The etherification or esterification may take place during or after polymerization. The lubricating composition may contain oxidation inhibitors, e.g. phenyl-b -naphthylamine, corrosion inhibitors, e.g. organic acids capable of forming water-insoluble metal soaps, gelling agents, e.g. metallic soaps and extreme pressure agents.ALSO:Liquid polymers suitable as lubricants and having molecular weights from 150 to over 1500 are produced by heating at a temperature above - 25 DEG C. in the presence of a catalyst one or more ethers containing (a) epoxide, or (b) glycol substituents, in case (b) to a temperature between 150 DEG and 300 DEG C. Ethers specified are (a) glycidyl methyl, ethyl, propyl, isopropyl, allyl, n-butyl, sec.-butyl, tert.-butyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, and dodecyl ethers; 2,3-epoxy-4-methoxybutane, -4-ethoxybutane and -4-isopropoxybutane; 1,2-epoxy-3-methyl - 3 - methoxypropane, - 3 - methyl - 3 - butoxypropane, -3,3 - dimethyl - 3 - isopropoxypropane, - 3 - isopropyl - 3 - isopropoxypropane, -2-methyl-3-isopropoxypropane and -3-n-amyl-3-isopropoxypropane; and 4,5-epoxy-6-methyl-6-isopropoxyhexane; 1,2 - epoxy - 4 - methoxybutane, - 4 - isopropoxy - butane, - 5 - ethoxypentane and -4-methyl-5-tert.-butylpentane; and 2,3 - epoxy - 5 - isopropoxypentane: (b) 1,2-dihydroxy - 3 - methoxypropane and - 4 - isopropoxybutane, 2,3 - dihydroxy - 5 - butoxypentane, 1,3-dihydroxy-4-methoxybutane and 2,4-dihydroxy - 5 - isopropoxypentane; 1,3 - dihydroxy-2-methoxymethylpropane and 1,4-dihydroxy - 3 - isopropoxymethylbutane. Suitable catalysts for (a) are sodium and potassium hydroxides, stannic and aluminium chlorides and boron trifluoride and its ether complexes; for (b) are iodine, hydrogen chloride, bromide and iodide, sulphuric acid, p-toluenesulphonic acid, benzene sulphonic acid, sodium bisulphate, aluminium sulphate and potassium acid sulphate. Polymerization may be effected in liquid, solution, emulsion or gaseous phases. Methane, ethane, propane, butane, dihydronaphthalenes, cycloheptane, 2-methylnonane, 2,6-dimethyloctane, 2,2,3-trimethylpentane, 2-methyl-3-ethylpentane, 2-methyloctane, 2,4-dimethylheptane, 4 - ethylheptane, dihexyl, 2,4,5,7-tetramethyloctane and water may be present. Additional reactants, e.g. methyl alcohol, ethylene glycol, amyl mercaptan, diisopropylamine and bis-(b -hydroxyethyl)-sulphide may be present to react with the p terminal hydroxyls. After removal of catalyst, the polymer is dehydrated, e.g. by distillation under reduced pressure and, if desired, decolourized by bleaching, hydrogenation using Raney nickel, nickel sulphide, copper, palladium or platinum catalysts, or by percolation of a solution in benzene, toluene, xylene or hexane through fuller's earth. The terminal hydroxyl groups may be etherified by methyl bromide or iodide, ethyl chloride, propyl iodide, benzyl chloride, methyl-benzyl chloride, methoxyethyl chloride, sodium monochloracetate or allyl chloride in the presence of sodium hydroxide, liquid ammonia or quaternary ammonium bases or salts; or esterified with formic, acetic, propionic, butyric, hexoic, 2-ethylhexoic, lauric, stearic, myristic, palmistic and capric acids in the presence of sulphuric or phosphoric acids. The etherification or esterification may take place during or after polymerization. The lubricating composition may contain oxidation inhibitors, e.g. phenyl - a - naphthylamine, corrosion inhibitors, e.g. organic acids capable of forming water-insoluble metal soaps, gelling agents, e.g. metallic soaps and extreme pressure agents.
GB25976/47A 1946-09-30 1947-09-24 Lubricating compositions Expired GB642255A (en)

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0397037A2 (en) * 1989-05-08 1990-11-14 Idemitsu Kosan Company Limited Use of polyoxyalkylene glycol derivative in lubricating oil for compression-type refrigerators.
GB2259711A (en) * 1991-09-20 1993-03-24 Nsk Ltd Rolling bearing lubricant
US5282689A (en) * 1991-09-20 1994-02-01 Nsk Ltd. Rolling bearing
US5385412A (en) * 1991-09-20 1995-01-31 Nsk Ltd. Rolling bearing
WO2007141248A1 (en) * 2006-06-02 2007-12-13 Freie Universität Berlin Process for preparing linear, methylated polyglycerol derivatives and their use for functionalizing surfaces

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE930102C (en) * 1952-11-08 1955-07-11 Bayer Ag Lubrication of refrigeration systems
DE1115394B (en) * 1956-08-03 1961-10-19 Ethyl Corp lubricant
DE1057715B (en) * 1956-11-07 1959-05-21 Bayer Ag Lubricating greases

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0397037A2 (en) * 1989-05-08 1990-11-14 Idemitsu Kosan Company Limited Use of polyoxyalkylene glycol derivative in lubricating oil for compression-type refrigerators.
EP0397037A3 (en) * 1989-05-08 1990-12-27 Idemitsu Kosan Company Limited Lubricating oil for compression-type refrigerators and polyoxyalkylene glycol derivative
US5269955A (en) * 1989-05-08 1993-12-14 Idemitsu Kosan Co., Ltd. Lubricating oil for compression-type refrigerators and polyoxyalkylene glycol derivative
GB2259711A (en) * 1991-09-20 1993-03-24 Nsk Ltd Rolling bearing lubricant
FR2681655A1 (en) * 1991-09-20 1993-03-26 Nsk Ltd ROLLING BEARING.
US5282689A (en) * 1991-09-20 1994-02-01 Nsk Ltd. Rolling bearing
US5385412A (en) * 1991-09-20 1995-01-31 Nsk Ltd. Rolling bearing
GB2259711B (en) * 1991-09-20 1995-07-05 Nsk Ltd Rolling bearing
WO2007141248A1 (en) * 2006-06-02 2007-12-13 Freie Universität Berlin Process for preparing linear, methylated polyglycerol derivatives and their use for functionalizing surfaces

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DE896415C (en) 1953-11-12
NL67705C (en)

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